Editors' Picks

Extreme Vacation Homes

Miami, Whistler, Thailand and Malibu

From a Miami mansion right on the beach, to a Whistler estate nestled high in the mountains, to a hidden retreat in the jungles of Thailand to a candy-colored hideaway in the Malibu hills, we'll explore the world's most extreme vacation homes.

Natural Balance House, San Juan Island, WA

Just off the coast of Washington, the remote San Juan Islands represent the best the Pacific Northwest has to offer -- vast evergreen forests, quaint fishing villages and scenic waterways. Built in 2008 by owner Glen Bruels, and dubbed the “Natural Balance House,” this 3,600-square-foot, eco-friendly home is built on a steep, rocky bluff overlooking the water. 9601280

Just off the coast of Washington, the remote San Juan Islands represent the best the Pacific Northwest has to offer -- vast evergreen forests, quaint fishing villages and scenic waterways. Built in 2008 by owner Glen Bruels, and dubbed the “Natural Balance House,” this 3,600-square-foot, eco-friendly home is built on a steep, rocky bluff overlooking the water.

Azzurra Castle, Grenada

Azzurra Castle, Grenada

Perched on the tip of a peninsula surrounded by blue waters of the Caribbean’s idyllic island of Grenada, the 26,000-square-foot, Moroccan-inspired Azzurra Castle has 6 bedrooms, a private turret apartment, a pool and 2 private beaches. Travelers looking for the ultimate, extreme vacation home can experience the castle’s luxury at $15,000 per week. 9601280

Perched on the tip of a peninsula surrounded by blue waters of the Caribbean’s idyllic island of Grenada, the 26,000-square-foot, Moroccan-inspired Azzurra Castle has 6 bedrooms, a private turret apartment, a pool and 2 private beaches. Travelers looking for the ultimate, extreme vacation home can experience the castle’s luxury at $15,000 per week.

Villa Philipson, Tuscany, Italy

Villa Philipson, Tuscany, Italy

Built in 1893 in the heart of Tuscany, Italy, the $50 million, 50,000-square-foot Villa Philipson features 10 bedrooms, ornate furnishings and vast grounds, complete with stables, a pool, a guardhouse, aviary and winery with beautiful landscape views of the Tuscan countryside. Built in 1893, the villa combines Renaissance-inspired design with 19th-century innovations. 9601280

Built in 1893 in the heart of Tuscany, Italy, the $50 million, 50,000-square-foot Villa Philipson features 10 bedrooms, ornate furnishings and vast grounds, complete with stables, a pool, a guardhouse, aviary and winery with beautiful landscape views of the Tuscan countryside. Built in 1893, the villa combines Renaissance-inspired design with 19th-century innovations.

La Crete Fort, Jersey, United Kingdom

La Crete Fort, Jersey, United Kingdom

Built in 1834 on the British isle of Jersey, La Crete is a 19th- century fort that’s been converted into a vacation home like no other. Starting at $500 a night, the hotel offers guests the chance to soak up centuries of military history, while exploring the island’s beautifully rugged cliffs and isolated beaches. 9601280

Built in 1834 on the British isle of Jersey, La Crete is a 19th- century fort that’s been converted into a vacation home like no other. Starting at $500 a night, the hotel offers guests the chance to soak up centuries of military history, while exploring the island’s beautifully rugged cliffs and isolated beaches.

Villa Gamberaia, Florence, Italy

Villa Gamberaia, Florence, Italy

Tucked in the hills of Florence, Italy, Villa Gamberaia is a sprawling 40,000-square-foot estate with panoramic views of Florence and the Tuscan countryside. The 17th-century estate features expansive grounds, including award-winning gardens, lemon and olive groves, 2 pools and a chapel -- complete with its own priest. The estate can be rented for $36,500 per week, including staff. For something more manageable, rent one of the property’s 4 guesthouses starting at $3,900 per week. 9601280

Tucked in the hills of Florence, Italy, Villa Gamberaia is a sprawling 40,000-square-foot estate with panoramic views of Florence and the Tuscan countryside. The 17th-century estate features expansive grounds, including award-winning gardens, lemon and olive groves, 2 pools and a chapel -- complete with its own priest. The estate can be rented for $36,500 per week, including staff. For something more manageable, rent one of the property’s 4 guesthouses starting at $3,900 per week.

Montauk, Hamptons, NY

Montauk, Hamptons, NY

Known for its romantic coastal beauty and old-fashioned charm, Montauk, in the Hamptons, is home to a 5,000-square-foot 21st-century masterpiece that overlooks more than 350 feet of white sandy beach. Built between 2002 and 2006, the $30 million estate sits on 4 acres of waterfront property, and features an infinity pool, a state-of-the-art screening room and a hi-tech gym. 9601280

Known for its romantic coastal beauty and old-fashioned charm, Montauk, in the Hamptons, is home to a 5,000-square-foot 21st-century masterpiece that overlooks more than 350 feet of white sandy beach. Built between 2002 and 2006, the $30 million estate sits on 4 acres of waterfront property, and features an infinity pool, a state-of-the-art screening room and a hi-tech gym.

East Sister Rock Island, Miami

East Sister Rock Island, Miami

Located just a few hours south of Miami, East Sister Rock is a small, privately owned island with 1 residence -- a 5,000-square-foot Bahamian-style bungalow with a wraparound veranda and panoramic ocean views. Built in the 1960s by owner Bob Williford, the beach house features 3 bedrooms, 2 bathrooms, a boat dock, pool and plenty of spaces to relax and soak up the sun. Guests looking to enjoy a secluded slice of paradise can rent the island for about $5,000 a week. 9601280

Located just a few hours south of Miami, East Sister Rock is a small, privately owned island with 1 residence -- a 5,000-square-foot Bahamian-style bungalow with a wraparound veranda and panoramic ocean views. Built in the 1960s by owner Bob Williford, the beach house features 3 bedrooms, 2 bathrooms, a boat dock, pool and plenty of spaces to relax and soak up the sun. Guests looking to enjoy a secluded slice of paradise can rent the island for about $5,000 a week.

Old Fort, Bequia, St. Vincent and the Grenadines

Old Fort, Bequia, St. Vincent and the Grenadines

Dating back to the 1700s, the Old Fort is one of the oldest buildings on Bequia, the second largest island in the Grenadines. Perched on a hilltop, with panoramic ocean views, the 18th- century plantation house sits on 28 acres of tropical landscape complete with fruit trees, an ancient sugar mill and a saltwater pool. For an unforgettable Caribbean getaway, guests can rent out individual rooms, as well as the entire property, for $8,000 to $12,000 a week. 9601280

Dating back to the 1700s, the Old Fort is one of the oldest buildings on Bequia, the second largest island in the Grenadines. Perched on a hilltop, with panoramic ocean views, the 18th- century plantation house sits on 28 acres of tropical landscape complete with fruit trees, an ancient sugar mill and a saltwater pool. For an unforgettable Caribbean getaway, guests can rent out individual rooms, as well as the entire property, for $8,000 to $12,000 a week.

Mount Hartman Bay Estate, Grenada

Mount Hartman Bay Estate, Grenada

Tucked away on the southern coast of the Caribbean isle of Grenada, near the capital St. Georges, Mount Hartman Bay Estate (“The Cave House”) is a sprawling 30,000-square-foot, 7-bedroom mansion built directly into the hillside. Complete with an indoor waterfall, 4-bedroom beachfront guesthouse, infinity pool, private beach, speedboat and helipad, the estate could be straight out of a Bond movie. Operating today as a 12-room hotel, the property treats guests to a luxurious getaway for $300 to $400 a night, or they can rent the entire estate for $7,900 a day.9601280

Tucked away on the southern coast of the Caribbean isle of Grenada, near the capital St. Georges, Mount Hartman Bay Estate (“The Cave House”) is a sprawling 30,000-square-foot, 7-bedroom mansion built directly into the hillside. Complete with an indoor waterfall, 4-bedroom beachfront guesthouse, infinity pool, private beach, speedboat and helipad, the estate could be straight out of a Bond movie. Operating today as a 12-room hotel, the property treats guests to a luxurious getaway for $300 to $400 a night, or they can rent the entire estate for $7,900 a day.

Villa Joya, Florence, Italy

Villa Joya, Florence, Italy

Located just 15 minutes from downtown Florence, Italy, is the romantic oasis known as Villa Joya. Surrounded by breathtaking views of the Tuscan countryside, the charming house has 2 luxurious bedroom suites, a pool, and an outdoor kitchen and living space, complete with a retractable movie screen. For $10,000 a week, guests can enjoy a romantic getaway as they sip wine and watch movies under the stars. 9601280

Located just 15 minutes from downtown Florence, Italy, is the romantic oasis known as Villa Joya. Surrounded by breathtaking views of the Tuscan countryside, the charming house has 2 luxurious bedroom suites, a pool, and an outdoor kitchen and living space, complete with a retractable movie screen. For $10,000 a week, guests can enjoy a romantic getaway as they sip wine and watch movies under the stars.

Soneva Kiri Resort & Spa, Koh Kood Island, Thailand

Soneva Kiri Resort & Spa, Koh Kood Island, Thailand

Located on the ultra-exclusive island of Koh Kood in southeastern Thailand, Soneva Kiri Resort & Spa features a handful of highly customized private residences on its 200-acre property for guests wanting to own their own piece of paradise. One of the resort’s most luxurious properties is the 5-bedroom “Hill Villa” -- a Zen retreat nestled deep in the lush tropical forests, complete with an infinity pool and panoramic views of the Bay of Thailand. The cost to own one of these properties starts at $3.25 million.9601280

Located on the ultra-exclusive island of Koh Kood in southeastern Thailand, Soneva Kiri Resort & Spa features a handful of highly customized private residences on its 200-acre property for guests wanting to own their own piece of paradise. One of the resort’s most luxurious properties is the 5-bedroom “Hill Villa” -- a Zen retreat nestled deep in the lush tropical forests, complete with an infinity pool and panoramic views of the Bay of Thailand. The cost to own one of these properties starts at $3.25 million.

Arc House, Hamptons, NY

Arc House, Hamptons, NY

Inspired by an old airplane hangar, the “Arc House” is a 6,400-square-foot, ultra-modern home located in East Hampton. Half hidden underground, the house is composed of a 64-foot steel roof, eco-friendly materials and Zen landscaping. 9601280

Inspired by an old airplane hangar, the “Arc House” is a 6,400-square-foot, ultra-modern home located in East Hampton. Half hidden underground, the house is composed of a 64-foot steel roof, eco-friendly materials and Zen landscaping.

Fustic House, Barbados

Fustic House, Barbados

Located in the northern-most parish of St. Lucy in southeastern Barbados, Fustic House is the largest private estate on the island. The 11-acre property features 4 sprawling residences, including the 18th-century Great House built from local coral stone, a library and a one-of-a-kind swimming pool built to appear like a natural lagoon. For $3,700 a week, guests can enjoy a luxurious island hideaway. 9601280

Located in the northern-most parish of St. Lucy in southeastern Barbados, Fustic House is the largest private estate on the island. The 11-acre property features 4 sprawling residences, including the 18th-century Great House built from local coral stone, a library and a one-of-a-kind swimming pool built to appear like a natural lagoon. For $3,700 a week, guests can enjoy a luxurious island hideaway.

Marisol Malibu, Malibu, CA

Marisol Malibu, Malibu, CA

Marisol Malibu, located just off Pacific Coast Highway in Malibu, CA, is an 80-acre community with cutting-edge landscaping and design, and panoramic ocean views of the Pacific and Catalina Island. The community’s main attraction is the Showcase Estate -- a 6,700-square-foot, state-of-the-art mansion with 4 bedroom suites, spa-inspired bathrooms, a great room, bar and infinity pool. 9601280

Marisol Malibu, located just off Pacific Coast Highway in Malibu, CA, is an 80-acre community with cutting-edge landscaping and design, and panoramic ocean views of the Pacific and Catalina Island. The community’s main attraction is the Showcase Estate -- a 6,700-square-foot, state-of-the-art mansion with 4 bedroom suites, spa-inspired bathrooms, a great room, bar and infinity pool.

Trident Castle, Jamaica

Trident Castle, Jamaica

One of the largest private residences in Jamaica, Trident Castle is nestled on a 7-acre estate perched atop a rocky cape. Built in the 1980s, the 40,000-square-foot estate has 8 bedroom suites, a grand ballroom with 47-foot ceilings, and a swimming pool and terrace with panoramic views of the seaside. For a price tag between $3,500 and $7,500 a night, guests can experience a fantasy vacation in a castle of their own. 9601280

One of the largest private residences in Jamaica, Trident Castle is nestled on a 7-acre estate perched atop a rocky cape. Built in the 1980s, the 40,000-square-foot estate has 8 bedroom suites, a grand ballroom with 47-foot ceilings, and a swimming pool and terrace with panoramic views of the seaside. For a price tag between $3,500 and $7,500 a night, guests can experience a fantasy vacation in a castle of their own.

The Masterpiece, Hong Kong

The Masterpiece, Hong Kong

Located in the heart of Hong Kong is the 67-story skyscraper known as “The Masterpiece.” At the top of the building is a 2-story luxury retreat that has 360-degree panoramic views of Hong Kong and nearby Victoria Harbor. Designed with elegance in mind, this retreat provides the ultimate vacation escape from the hustle and bustle of one of the busiest cities in the world. 9601280

Located in the heart of Hong Kong is the 67-story skyscraper known as “The Masterpiece.” At the top of the building is a 2-story luxury retreat that has 360-degree panoramic views of Hong Kong and nearby Victoria Harbor. Designed with elegance in mind, this retreat provides the ultimate vacation escape from the hustle and bustle of one of the busiest cities in the world.